The only upside of Windows, and definitely a major one, is power management. On Ubuntu, my battery lasts around 2.5h with moderate use whereas on Windows, it's around 3-4 hours. Yes, I am already using powertop and TLP. =)
In truth I don't like any current OS - when you add up all the pros and cons, Linux has the best overall balance of attributes for my use. It's far from optimal though. I find the state of OSs in 2020 pretty sad.
On Windows I would have vaguely but very briefly googled. I would either find a quick fix or not, and be on my way.
On Ubuntu I only bother searching online if I know what software's causing it, and it's open source. Otherwise I find the signal/noise ratio too high (and I rarely get useful answers on SO or other forums - I either get nothing or too many people helpfully but uselessly saying "try this!" "try that!"). More often I just dig into things myself.
So I trawled the syslog, couldn't initially find anything, narrowed down by triggering the issue deliberately while `journalctl -f`'ing, etc. I traced the problem to a recently installed Gnome extension that was crashing X on screen blanking. An uninstall failed so I had to find out where extensions are on the filesystem, remove it manually, restart mutter, etc.
The whole thing took about 25 mins.
The upside for Ubuntu here is that I could actually fix the issue. This is rarely a given with Windows (though for me it produces fewer such small issues). On Windows, if I can't fix something that's not critical within a few minutes, I end up just putting up with it. These accumulate over time and I find the OS increasingly irritating. Ubuntu's irritation level doesn't increase over time (though its plateau is way above zero). The downside for Ubuntu is that this really does involve more fiddling time (a known known because I keep logs). For me (a regular non-expert user) anyway.
But there's no doubt I've spent at least 10x as much time on Ubuntu configuring and reading and fixing.